The present invention relates to an aromatic bleaching agent composition and more particularly to an aromatic bleaching agent composition comprising a 1-substituted-2,2,4-trimethylpentane-3-one derivative.
In recent years, with the diversification and spread of hygienic materials, etc. and the appearance of new killer colon bacilli, including coliform bacillus O-157, the term xe2x80x9canti-bacterialxe2x80x9d or xe2x80x9cdisinfectantxe2x80x9d has spread even among general consumers. Under these circumstances, today, the presence of chlorine-based bleaching agents having bactericidal action is indispensable to extermination of bacteria, vicious microorganism, fungi and acari present close to human beings.
In order to meet the consumers"" need for bleaching agent which can be used not only to remove stain such as spot, yellowing and darkening from daily clothing for the purpose of meeting their liking for cleanliness as in the foregoing circumstances as well as for colored or figured clothing, an oxygen-based bleaching agent appeared on the market. Today, it is also true that the main role of the oxygen-based bleaching agent is to allow the color of the clothing to look sharp or prevent the clothing from yellowing or darkening during daily washing in addition to the conventional concept of bleaching or germicidal action. This oxygen-based bleaching agent is blended with proper surface active agents or bleaching activators to provide various washing detergents or household detergents which are widely used.
These bleaching agents can be used for many purposes as mentioned above but are disadvantageous in that they give out an offensive stimulating odor during use. For example, an aqueous solution of sodium hypochlorite, which is a typical chlorine-based bleaching agent, gives out a peculiar offensive stimulating odor. A bleaching agent containing potassium percarbonate or potassium perborate, which is an oxygen-based bleaching agent, gives out a stink characteristic to various bases incorporated therein. In order to overcome these defects in compliance with the wishes of the consumers, studies have so far been made of masking agent and perfume for aromatizing these bleaching agents.
The perfume and masking agent to be used for these purposes are subjected to restriction of chemical structure so that they stay in a stable condition in the bleaching agent components and undergo no reaction with the bleaching agent components to prevent themselves from deteriorating the effect of the bleaching agent components and from being decomposed by the bleaching agent components and hence showing deterioration or modification that lowers the commercial value thereof. For examples, those having an ether structure free of unsaturated bond (see JP-B-3-43320 (The term xe2x80x9cJP-Bxe2x80x9d as used herein means an xe2x80x9cexamined Japanese patent publicationxe2x80x9d)), those having specific alcohol and ester structures (see JP-B-3-29280 and JP-A-2-166200 (The term xe2x80x9cJP-Axe2x80x9d as used herein means an xe2x80x9cunexamined published Japanese patent applicationxe2x80x9d)), etc. are known for their effectiveness. Chemical structures which are subject to chemical change under some alkaline conditions of base or upon the oxidative effect of bleaching agent, i.e., unsaturated bond, alcohols, aldehydes and ketones have been normally considered inappropriate.
On the other hand, among ketones, 1-phenyl-2,2,4-trimethyl-3 pentanone is known as a 1-substituted-2,2,4-trimethylpentane-3-one derivative which can be blended as a perfume component to provide a metallic and green rosy fragrance (see JP-A-63-203609). Further, as a compound having a geranium-like, rosy and spicy rosinol-like fragrance there is known 1-cyclohexyl-2,2,4-trimethyl-3-pentanone (see JP-A-63-203643) It is described that these compounds can be used to aromatize quality mixed perfume, perfume, soap, shampoo, hair rinse, detergent, cosmetics, hair spray, aromatic, etc.
However, the above cited patents have neither reference to the chemical stability of these compounds nor suggestions to the fact that these ketones exhibit a high stability particularly to bleaching agent against the conventional recognition. More specifically, there are no suggestions to the fact that 1-substituted-2,2,4-trimethylpentane-3-one derivatives are unprecedentedly extremely rare ketones which stay in a chemically stable condition in both a chlorine-based bleaching agent and an oxygen-based bleaching agent without deteriorating the bleaching activity thereof and thus show no deterioration of fragrance and a high masking effect. Further, there are no suggestions to the fact that an aromatic bleaching agent composition containing 1-substituted-2,2,4-trimethylpentane-3-one derivative has a remarkably high commercial value.
As previously mentioned, the recent trend is that bleaching agent components are incorporated not only in specific bleaching agents but also in daily washing detergents, etc. Accordingly, there is a growing demand for the development of a chemically stable masking agent which can be used for these purposes without deteriorating the bleaching agent components or bases. Therefore, the development of such a masking agent is very useful particularly for the art of hygienic materials, detergents, etc.
It is therefore an object of the present invention to provide a chemically stable bleaching agent composition which can exert an excellent masking effect without deteriorating the bleaching agent base.
The inventors made extensive studies of a compound which exhibits an extremely high stability even in a bleaching agent having a strong oxidative effect. As a result, it was found that a 1-substituted-2,2,4-trimethylpentane-3-one derivative is extremely stable in such a bleaching agent and has a high masking effect and an aromatic bleaching agent composition comprising such a derivative incorporated therein has a remarkably high commercial value. The present invention has thus been worked out.
The present invention provides an aromatic bleaching agent composition comprising one or more 1-substituted-2,2,4-trimethylpentane-3-one derivatives represented by the following general formula (1): 
wherein X represents a benzene ring or a cyclohexane ring; and R represents an arbitrary hydrogen atom on said ring or a methyl group which substitutes said hydrogen atom.
It is known that ketones normally exhibit a high reactivity and thus undergo a polymerization reaction such as aldol reaction in the presence of an alkali. It is also known that when acted upon by a peracid, ketones undergo nucleophilic reaction that leads to Baeyer-Villiger oxidation resulting in the production of esters (Synthesis, pp. 1324-1347, 1995). However, the 1-substituted-2,2,4-trimethylpentane-3-one derivative to be used in the invention is present in an extremely stable condition even against the alkalinity of an aqueous solution of sodium hypochlorite or upon the oxidation by sodium hypochlorite or alkaline metal salt of percarbonic acid or perboric acid because of its structurally specific and high steric hindrance. The 1-substituted-2,2,4-trimethylpentane-3-one derivative doesn""t modify or deactivate these bleaching agent components and thus exerts an excellent effect of masking the odor of the bleaching agent base. It can be thus said that an aromatic bleaching agent composition having such a 1-substituted-2,2,4-trimethylpentane-3-one derivative is very useful.
The synthesis of the 1-substituted-2,2,4-trimethylpentane-3-one derivative to be used in the invention can be accomplished by a process which comprises allowing a base such as hydroxide of alkaline metal (e.g., sodium hydroxide) or hydride of alkaline metal (e.g., hydrogenated sodium) to act on diisopropyl ketone, and then adding benzyl chloride to the material, as described in JP-A-63-203609 if R and X in the general formula (1) are hydrogen atom and benzene ring, respectively.
Alternatively, if R is a hydrogen atom and X is a cyclohexane ring, the synthesis of the 1-substituted-2,2,4-trimethylpentane-3-one derivative to be used in the invention can be accomplished by a process which comprises synthesizing the foregoing compound wherein X is a benzene ring, and then hydrogenating the benzene ring of the foregoing compound in the presence of a known hydrogenation catalyst such as palladium-carbon catalyst as described in JP-A-63-203643.
Alternatively, if R is a methyl group, methyl-substituted benzyl chloride, which corresponds to benzyl chloride, can be used for the synthesis of the 1-substituted-2,2,4-trimethylpentane-3-one derivative. The synthesis process as mentioned above is an example of the processes for the synthesis of the compound of the invention and thus doesn""t restrict the process for the synthesis of the compound of the invention.
Some of the compounds to be used in the invention have asymmetric carbon atoms and hence an optically active material in its molecule depending on the kind of the substituents thereon. The problems that the present invention is to solve are only the chemical stability of the compound of the invention to a main bleaching agent component such as aqueous solution of sodium hypochlorite, alkaline metal salt of percarbonic acid and alkaline metal salt of perboric acid and the effect of the compound of the invention on these components. Accordingly, optically active compounds in d-isomer and l-isomer, mixture thereof, and racemic modification may be used without any difference. Possible compounds having a plurality of asymmetric carbon atoms per molecule may be used singly or in admixture of two or more thereof in the present invention.
The 1-substituted-2,2,4-trimethylpentane-3-one derivatives of the invention may be used singly. Alternatively, one or more of these 1-substituted-2,2,4-trimethylpentane-3-one derivatives may be used in admixture with commonly used perfume components to give a perfume composition. As the commonly used perfume components there may be used those described in, e.g., Arctander S., Perfume and Flavor Chemicals, published by the author, Motclair, N.J. (USA), 1969. Among these perfume components, compounds stable to bleaching agent component described in JP-B-3-43320 and JP-B-3-29280 are effectively used.
The amount of the 1-substituted-2,2,4-trimethylpentane-3-one derivative to be used in the invention can be properly determined depending on the purpose, working conditions, etc. In practice, however, it is from 0.001 to 50% by weight, preferably from 0.01 to 20% by weight, more preferably from 0.02 to 1.0% by weight based on the weight of the bleaching agent composition.
Examples of the bleaching agent component employable herein include chlorine-based bleaching agent component such as aqueous solution of sodium hypochlorite and aqueous solution of calcium hypochlorite, and oxygen-based bleaching agent component such as sodium percarbonate, potassium percarbonate, sodium perborate, potassium perborate and hydrogen peroxide. Examples of calcium hypochlorite include bleaching powder, which can be dissolved in water to produce calcium hypochlorite in the system. The percarbonate and perborate may be used in the form of solid, aqueous solution or the like. The aromatic bleaching agent composition of the invention is not specifically limited to these bleaching agent components, etc. The aromatic bleaching agent composition of the invention may be a hypochlorite, percarbonate and perborate other than mentioned above, peracid such as peracetic acid, adduct thereof or isocyanurate in the form of solid or aqueous solution. The masking agent to be used stays stable also in the product comprising these components and has no effect on the bleaching agent components.
A bleaching agent composition normally comprises as a bleaching activator tetraacetyl ethylene diamine, tetraacetyl glycol uryl, pentaacetyl glycose, cyanamide, cyanopyridines, isophthalonitrile, nonanoyloxybenzenesulfonic acid, piperidine, piperidine derivative, morpholine derivative, hexamethyleneimine derivative, diazabicycloheptanoyl derivative, nonheterocyclic N-haloamine compound or the like incorporated therein to further enhance the activity of the bleaching agent. The masking agent of the invention stays stable even in the presence of these bleaching activators. The bleaching activator is not specifically limited to the foregoing compounds.
Further, the aromatic bleaching agent composition of the invention, if it is a detergent, may comprise a commonly used surface active agent, builder, recontamination inhibitor, rinsing improver, viscosity adjustor, enzyme, softening agent, fluorescent agent or dye incorporated therein to further enhance detergent properties without any hindrance.
The aromatic bleaching agent composition product of the invention may be in any form such as liquid, gel, mass, tablet, powder, granule, capsule and microcapsule but the present invention is not limited thereto. Examples of the aromatic bleaching agent composition include compositions containing the foregoing bleaching agent components as an effective component such as household detergents, e.g., detergent for kitchen, detergent for bathroom, detergent for toilet, detergent for household furniture and detergent for drain pipe, washing detergents, e.g., detergent for clothing and detergent for shoes, disinfectants, germicides, mildewproofing agents and decolorizers.